Summary
Navy Pier's Halloween season centers on Slightly Spooky Saturday, a free, family-friendly day of trick-or-treating on Saturday, October 31, 2026, from 12 to 6 p.m. The same weekend, Festival Hall at Navy Pier hosts Dom Dolla for two nights, October 30 and 31, an 18+ ticketed show that will add extra crowds and energy to the Pier. The Pier's bars also host a Halloween Bar Fest for guests 21 and up, and nearby Roberts Pizza & Dough Co. runs its annual Howl-O-Ween dog costume contest. Costumes are welcome aboard, so a Chicago boat tour is an easy way to build a Shoreline Sightseeing cruise into your Halloween weekend, whether you're heading to the Pier before or after.
Table of Contents
- Navy Pier Halloween Events at a Glance
- Slightly Spooky Saturday: Free Family Trick-or-Treating
- Dom Dolla at Festival Hall: October 30-31
- Navy Pier Halloween Bar Fest: A 21+ Halloween Crawl
- Howl-O-Ween at Roberts Pizza & Dough Co.
- See Navy Pier’s Skyline From the Water This Halloween
- Planning More of Your Fall Trip to Chicago
- Book Your Halloween Weekend Cruise
- Frequently Asked Questions
Come to Navy Pier dressed in your best costume for trick-or-treating, Halloween festivities, and boat rides. Shoreline Sightseeing runs two Chicago boat tours right from Navy Pier, the Skyline Lake Tour and the Architecture River Tour, making either an easy add-on to a day of Halloween activities.
Navy Pier Halloween Events at a Glance
| Event | Date | Time | Audience |
|---|---|---|---|
| Slightly Spooky Saturday | Saturday, October 31, 2026 | 12:00 p.m. – 6:00 p.m. | Free, all ages |
| Dom Dolla at Festival Hall | Friday, October 30 & Saturday, October 31, 2026 | 5:00 p.m. start | 18 and up, ticketed |
| Navy Pier Halloween Bar Fest | Late October / early November | Afternoon into evening | 21 and up, ticketed |
| Roberts Pizza & Dough Co. Howl-O-Ween | Late October | Afternoon | Free, dogs and their owners |
| Shoreline Sightseeing Boat Tours | Daily throughout October | Multiple daytime departures from Navy Pier | All ages, ticketed, costumes welcome |
Slightly Spooky Saturday: Free Family Trick-or-Treating
Navy Pier’s signature Halloween event is Slightly Spooky Saturday, a free day of trick-or-treating throughout the Pier on Saturday, October 31, 2026, from noon to 6 p.m. The event includes candy stops, live entertainment, festive workshops, and family-friendly activities for all ages, making it an easy centerpiece for a Halloween day downtown.
Dom Dolla at Festival Hall: October 30-31
Navy Pier’s Festival Hall hosts Grammy-nominated DJ, producer, and songwriter Dom Dolla for two nights over Halloween weekend, Friday, October 30 and Saturday, October 31, 2026, both starting at 5 p.m. It’s an 18-and-up ticketed show, separate from the free family programming earlier in the day, but it means the Pier will be busier than usual that Saturday, with both a family event and a major concert drawing crowds. If you’re planning a Halloween weekend visit, it’s worth building in extra time for parking and getting around, and a daytime boat tour is a good way to see the skyline before the evening crowds pick up.
Navy Pier Halloween Bar Fest: A 21+ Halloween Crawl
For guests 21 and up, Navy Pier’s Halloween Bar Fest turns several of the Pier’s bars and restaurants into a ticketed Halloween crawl, with past editions including Offshore Rooftop, Harry Caray’s Tavern, Margaritaville, Billy Goat Tavern, Bar Sol Mariscos, and Reunion by Chef Art Smith. One ticket typically grants access across the participating venues. Since exact dates and participating bars can shift year to year, check Navy Pier’s current event listings before buying tickets.
Howl-O-Ween at Roberts Pizza & Dough Co.
A short walk from the Pier, Roberts Pizza & Dough Co. hosts its annual Howl-O-Ween dog costume contest, a free, family-friendly event with categories for scariest, cutest, and most creative costumes. Humans are welcome to dress up too, and the event typically includes dog treats, photo opportunities, and Halloween cocktails for the adults. It’s a fitting stop if you’re bringing a furry friend along for your Halloween weekend in Chicago.
See Navy Pier’s Skyline From the Water This Halloween
Shoreline Sightseeing operates two tours departing from Navy Pier, so there’s an option whether you want open water or river views.
The Skyline Lake Tour departs from 600 E. Grand Ave. and heads out onto Lake Michigan, cruising both north and south for skyline views that stretch from the Magnificent Mile and Streeterville past Millennium Park, Grant Park, and Museum Campus, with fares starting at $34.
The Architecture River Tour departs from a separate Navy Pier dock at 124 N. Streeter Drive, at the entrance to the Navy Pier boardwalk, and this departure point also offers easier wheelchair accessibility. Between costume contests, candy stops, and a sold-out concert crowd, either tour is a relaxed way to see the skyline from the water before the day gets busy, and cooler October weather makes for a comfortable ride.
Planning More of Your Fall Trip to Chicago
Halloween at Navy Pier is one piece of a bigger fall season downtown. For a broader look at what else is happening around the city this time of year, see Shoreline Sightseeing’s roundup of Chicago fall activities.
Book Your Halloween Weekend Cruise
Trick-or-treating, costume contests, a concert, and a bar crawl are all part of Navy Pier’s Halloween season this year. Check current schedules and book online with Shoreline Sightseeing to see the skyline from the water during your Halloween weekend visit.
Frequently Asked Questions
Slightly Spooky Saturday is Navy Pier’s free, family-friendly Halloween event, featuring trick-or-treating throughout the Pier, live entertainment, and festive workshops. In 2026, it takes place Saturday, October 31, from 12 to 6 p.m.
Yes. Dom Dolla performs at Festival Hall at Navy Pier on Friday, October 30 and Saturday, October 31, 2026, both nights starting at 5 p.m. It’s an 18-and-up ticketed show.
No. The Halloween Bar Fest is a 21-and-up, ticketed event across several of Navy Pier’s bars and restaurants. Check current listings for the exact date and participating venues.
Yes. Roberts Pizza & Dough Co., a short walk from the Pier, hosts an annual Howl-O-Ween dog costume contest that’s free to attend.
Both the Skyline Lake Tour and the Architecture River Tour depart from Navy Pier, from two separate docks. The Skyline Lake Tour heads out onto Lake Michigan, while the Architecture River Tour travels the Chicago River, and both run during Halloween weekend.
